Regenerate: The Art of Growing from Loss

A Conversation with Richard Banfield, Author/Creator

On January 1, 2014, Sahil Bloom wrote a letter to his future self. In it he wrote out 9 things he hoped for in the future. He opened that letter on January 1, 2024. I was captivated by this idea and saw it a few times at the turn of the year posted on social media. I love the idea of engaging with a future/past version of myself. 

As comments piled onto the post I read some of the more upvoted ones. Richard Banfield’s comment stood out,  “Before my wife died I wrote myself a letter. The letter was an attempt to counsel future-Richard on how to deal with the inevitable grief and loss. It's hard to describe how important that letter was for my healing and my family's future…” 

When I looked into Richard a little I learned more about who he was and decided to reach out for an interview. He was gracious enough to accept and we spoke a few days later on what turned out to be the 2 year anniversary of his wife's passing. I hope you find his experience as profound as I did.

Richard: First, I have to say, what you've done with your website, the illustrations are fantastic.

Rob: Thanks. Yeah, they're quite trippy.

Richard: No, they're very cool. Reminds me of this studio called Bad Breath or Morning Breath. They do quirky, polished, rich design stuff.

Rob: We're pretty happy with them. We hired an Indonesian illustrator, gave him some direction and rough copies, and he came up with these really cool things.

Richard: He's good. Introduce me, I've got a book in the works and need an illustrator.

Rob: Absolutely. The first stuff he gave us was too conservative. We told him to put more of himself in it, and he came back with these nuts, so crazy illustrations.

Richard: I'm from the deep south, South Africa, and moved here 23 years ago. I've been in the design, UX, and product space all that time. I'm one of the OGs of this space. Spent some time doing what you're doing, reaching out, acting like a journalist, gathering ideas, synthesizing them into books, talks, workshops. It's a big part of my day-to-day. Currently, I'm working on two books.

I'm still curious about what's going on. Lots of people are doing stuff, but I'm not sure many know if they're doing it right. So, I'm also curious about the same things you are.

Rob: Nice, thanks for sharing. I saw your LinkedIn post about writing a letter to yourself from the past. Your response moved me, especially about your wife. I have friends who've experienced similar things. It's challenging. Thank you for sharing. Could you give a synopsis of that experience, whatever you're comfortable with?

Richard: Yes, today marks the anniversary of Kristy’s passing. It's been two years. We were together for about 10 years. She found a lump in her breast when our youngest was still little. Unfortunately, that was just the tip of the iceberg. She had not only breast cancer but pancreatic cancer as well. It was due to a genetic mutation in her family, which we didn't know about at the time, but now we're all aware of it.

The whole experience brought out a kind of resilience in our family. In the letter I mentioned, I talked about this concept of anti-fragility, which we didn't invent but borrowed from Nassim Taleb, who wrote a book called "Antifragility." The idea is that predicting the future is futile. Speculating about next week's trends or what might happen to us individually is somewhat ludicrous because we just don't have control over it.

Christie and I embraced that concept, deciding to be prepared rather than predictive. That's become a theme in my life now. While she was sick, I used art as a way to process our situation. For example, I painted peonies. We have peonies that get destroyed in the winter, but every year they come back bigger and brighter. That became a metaphor for us – the idea that you can be knocked down but then rise again, even stronger.

This idea of being vulnerable yet resilient has stuck with me, not just in my personal life but professionally as well. I strive to be generative rather than consumptive. Taking an anti-fragile approach means building something that, even if broken by change, comes back better. It's an interesting perspective for product development, right? Instead of trying to make a product perfect, make it adaptive. The same goes for team building. Instead of fixating on a rigid roadmap, create an adaptive environment and team that can flexibly respond to changes, as we've seen with COVID and market fluctuations.

I strive to be generative rather than consumptive.

With the unpredictability we've seen, like the pandemic or inflation, the key is building something that adapts and improves through these challenges.

So, I think building a team with antifragility as its foundation is key. There are principles to this, and I won't bore you with them now, but you can find them in the book. I apply these principles in both my personal and professional life.

Rob: Definitely going to look into that. It resonates with me. I feel like many teams focus so much on the plan that they lose sight of their purpose. The plan should be flexible, but the destination or purpose should be well-defined. I love working with teams where everyone brings different skills. It's like being in a band, not an assembly line. We should play together, not work in a linear fashion.

Richard: I’m going to quote you on that.

Core Principles

Rob: This idea of syncing as a team is something I’ve really come to appreciate. Even though I’m not a great musician, playing music with others is a great example of this. When you jam together, someone might come up with a riff that you couldn’t have thought of alone. That's the kind of collaborative environment I’m really interested in. Through my experiences, I’m continually trying to improve this approach. What about you, Richard? Do you have a core principle or value that guides your work on products?

Richard: In a sentence, it's "mess around and find out." I started thinking I'd be a biologist, studying the scientific method. I became enamored with the idea that you can experiment your way to answers, showing up with nothing but curiosity. When I entered the business world, it was almost the opposite. Experts were revered as the only source of truth, whether because they wrote a book, led a successful company, or were articulate. Many of these experts didn't represent the diversity I saw in the marketplace. A lot of them were older white guys saying, "I took my company to a billion dollars, so it should work for you too." Growing up, people like Jack Welch and Andy Grove were considered brilliant. But on closer inspection, many of these guys were actually quite harmful, not just to their organizations in terms of share prices, but they also left a generation of people in their wake. The people of that generation were damaged; they were terrible managers and leaders because they tried to emulate people like Jack Welch. 

Coming into business with a scientific mindset means adopting a humble approach. You assume you don't know everything and that you'll learn along the way. You focus on asking good questions, which eventually evolved into what's now known as design sprints.

The five or six steps of the design sprint were later formalized by Jake Knapp and the team at Google Ventures. Through a friend, Rich Miner, who sold Android to Google, I was introduced to them. They were busy, so a few of us wrote a book called "Design Sprint."

That book became a bestseller. It was great timing – design was becoming popular, and product management was gaining importance. We called it the 'answer machine' – you input questions, run experiments, and get answers, all within a short time frame.

It was a validation of the idea of 'messing around and finding out.' It's not just a catchy phrase; it's effective for business and knowledge. Teams can quickly adapt to this state of curiosity, which is healthier and opens up possibilities.

This approach aligns well with antifragility, where one of the principles is to reduce risk through experimentation and creating options. It's been practical for me. I've launched successful projects quickly, even as a dyslexic. I wrote a book using the design sprint methodology. We locked ourselves in a room for a week with questions and ended up with the book. We've used it as a consulting methodology, to open doors for new customers, and solve problems. 

At InVision, we used it to launch products. With a product called InVision Learn, we went from concept to 1.5 million dollars in pipeline and about 700,000 in actual revenue in just 10 months.

It shows the power of creating micro-experiments and learning fast. There's a lot of talk about moving fast and breaking things, but I prefer a more scientific approach. We don't always need to move fast or break things. It's about trying new things, staying open and curious. That principle has held true for me for the last 20 years.

Rob: That's awesome. I've noticed in my consulting experience, especially with larger companies, they can spend ages on business analysis, trying to make the 'right' decisions. They deliberate for months, maybe a year, when they could have explored all the options in that time. It's frustrating to see so much time wasted on decisions with no real evidence.

Richard: Exactly. It's like when you're running an agency or consultancy, like you are now. You need a process like a design sprint, or something similar, to bring your customers into the process in a low-risk way.

Keep in mind, regardless of how customers communicate their needs, they judge you on timely and on-budget delivery. They might say they chose you for your creativity, your style, maybe even your facial hair, but in the end, they need to justify the spending to their bosses.

That's why you need something that allows clients to see the value of your work quickly. The design sprint was our way of opening doors, showing clients that there are answers and we can move forward, sometimes even advising them to stop spending on a wasteful venture. They'll still spend with you, just in a different, more effective way.

Tracing History 

Rob: I love that. So, next, I'm curious about the origin of your approach. It’s like the scientific method, moving quickly, breaking things, but in a measured, meaningful way. Where does this come from for you? You mentioned studying marine biology in university, but why were you interested in that field in the first place?

Richard: The answer might be disappointing because there's no direct thread. I chose marine biology because I was working as a scuba diving instructor on a remote island in the Indian Ocean. I became obsessed with the marine life there and the changes I was observing, especially with coral reefs becoming victims of overfishing and exploitation. I wanted to see if there was something I could do about that.

I briefly thought about becoming a game ranger too, but there's really no continuous thread in my choices. My belief has always been that you shouldn't let schooling get in the way of your education. In my 20s, I lived what I now describe in design sprints. I tried different jobs, studied different subjects, traveled extensively, and just explored as much as I could. I didn't focus on building a career; I wanted to experience as many things as possible.

I lived my life in reverse, doing all the things people talk about doing when they retire – scuba diving in tropical locations, sailing, going on safaris in Africa. Along the way, I even started small businesses, like building futon bases when futons were popular.

Those futon mattresses needed bases, so I built them. I also had a t-shirt business and a bunch of other experimental ventures. These were ways for me to figure out what I loved, what I disliked, and what I never wanted to do again. I realized that the corporate world wasn't for me. Not that it's bad, it just wasn't my path.

My life became my original experiment, leading me to where I am today. Raised by amazing parents who wanted me to live a good life and explore my talents, I never knew where it would lead. But that's okay.

Now, I'm very in tune with what I love, what I want to do, and what makes me happy. Not just sitting-on-a-beach-with-a-margarita happy, but finding joy in the work I do, even the hard parts. Like I said to a friend, it's about the pursuit of happiness, not the acquisition. It's the struggle towards something rewarding that's gratifying.

Rob: Yeah, I love that. So, your parents allowed you the freedom to explore?

Richard: They hoped I'd eventually settle on something. I'm sure they worried I'd end up a homeless derelict! But those experiences, being far from home with little money and no job, they teach you. Before the internet and cell phones, you couldn't just call for help. You had to adapt and figure things out, becoming good at surviving. You learn to be resourceful.

Rob: Desperation can be the best inventor, right?

Richard: Absolutely, it's the mother of all invention.

Rob: Yeah, I love that. Today's technology has made things easier, but it also takes away the struggle. Like a caterpillar in a cocoon, it needs that struggle to become a butterfly. If you remove the cocoon too soon, it can't fly. The struggle, the pursuit, prepares you for what's next, and I really appreciate that perspective.

That experience... What did your parents do for work, if you don't mind me asking?

Richard: My mom was initially a primary school teacher, then shifted into the commercial world as a real estate agent. My dad, a salesperson who eventually started his own business, made jacuzzis and hot tubs. We witnessed their entrepreneurial journey, including the business's eventual failure due to poor investment choices. It was a valuable lesson in the ups and downs of entrepreneurship.

They were average in terms of perspectives, but extraordinary in giving us freedom to explore. Maybe it's because they were like hippies from the '70s.

Rob: How many siblings do you have?

Richard: Just one sister, a bit younger than me.

Rob: Where is she, and what does she do?

Richard: She's in the States, an author. Unlike me, she's not dyslexic - almost perfect, in fact.

Rob: What does she think of your writing?

Richard: I believe she's proud. It's exciting to see each other putting stuff out there.

Rob: Very cool. So, back to your 'scientific experiment' of life – what did you discover you definitely wanted to do and what you didn't?

Richard: I delved deep into biology, thinking of pursuing a PhD. But my supervisor pointed out my interest in people and diverse areas, which wouldn't suit the specialized nature of scientific research. The realization that marine biology involved more lab work than fieldwork was a turning point. I loved science but didn't want to be confined to a lab. These experiences help you distinguish between the idealized version of a career and its reality.

The U.S. education system pushes for specialization too soon. Students should explore a variety of subjects in their first years of college instead of being pressured to choose a specific path right away.

In university, I tried so many different things. I did archaeology, botany, physics, chemistry, and even dabbled in statistics and math, though I wasn't very good at that. Our education should be a melting pot of ideas and curiosities. We fail our kids by not offering this. The system needs a major overhaul to return to its original purpose: introducing people to different perspectives.

I decided not to pursue a career as a scientist, but I applied scientific principles to other interests. I started a side business in design after being asked to create packaging for a dairy product range. This was before Photoshop and Illustrator, so we just experimented with Corel Draw. That experience led me to start a design company, using the experimental approach I learned at university.

That design company was just the beginning. I ran it for 15 years, worked at InVision, and wrote several books. I don't see myself as an expert, more like a Malcolm Gladwell of our industry. I enjoy hearing people's stories, synthesizing them into books, workshops, keynote talks, and articles. Last year I published over a hundred articles. My interest lies in curiosity, asking questions. In design and product development, curiosity and experimentation are key. Hubris in this field gets exactly what it deserves.

As for consulting, it has its downsides, but what I love about it is the constant learning and the opportunity to apply diverse experiences to new challenges.

Rob: Yeah, that all resonates. I’ve appreciated my time as a consultant, despite the general reputation of consulting. It's not always viewed positively, but there's something rewarding about the variety and the challenge of the work.

That experience of not knowing how you'll learn something is exhilarating, like falling without knowing when you'll hit the ground. I appreciate hearing about your experiences. So, from that time, what is something you definitely knew you didn't want to do?

Richard: One thing that stands out is my decision to complete military service right after high school in South Africa. If you didn't go to university immediately, you had to serve. I finished high school at 17 and chose to get the service out of the way. It was both the best and worst of times. It was excruciatingly difficult but also showed me my true limits. However, by choosing to serve, I postponed my plans to attend art school, which I had originally thought I'd pursue.

I thought I was going to be an artist and had been accepted into art school, but I decided to postpone that and eventually drifted away from art, viewing it as something trivial. Rediscovering art later in life has been wonderful. It's therapeutic and recharges my creative batteries. As a consultant and advisor, I constantly give of myself, which can be draining. Art, both writing and visual, has become a way to recharge and experiment. It's been so fulfilling that I've created nearly a hundred pieces in the last few years.

Rob: Wow, I love that.

Richard: Yeah, art helps me maintain that experimental mindset. You start with an idea, but the act of creating art itself changes the artwork. It's been really exciting and has led to new opportunities. Some commissions came through. I did some charity work for a really interesting project, participated in public art displays, and some exhibition-type work, which I wasn't expecting. It wasn't part of the plan, but I think it was something that I postponed and ignored rather than decided not to do. I should have said, "I'm not going to do that now or yet," instead of closing that chapter. Keeping that door open has proved to be a really important part of my life right now.

Rob: Yeah, it sounds sort of cathartic in a lot of ways.

Richard: Yeah.

Advice to Aspiring Product Managers

Rob: Thank you for sharing. What would be your number one piece of advice for an aspiring product manager?

Richard: The framework I use is 'terrain, tools, and team.' First, map the terrain – understand what's actually going on. Product management is a contextually specific art, not a science. So, understand your terrain. Next, the tools – you need the right tools for your terrain. For me, it's using something like a design sprint, an experimental methodology to get answers. You need to test and validate a lot of assumptions, so you need mechanisms for that. And lastly, the team – it's about who's on the team and whether they understand their roles and are invested in them. These elements are all intertwined. If a product manager brings the approach from one company to another without considering context, they're likely to fail. It's like taking polar gear to the desert.

These are like a triad – terrain, tools, and team. The team is crucial. Who's on the bus, who's in the right seat, to use Jim Collins' analogy. Do they understand their roles and objectives? Are they self-aware, personally and professionally invested? What does their incentive structure look like? These elements are all intertwined.

Understanding the context and having the right tools allows you to make better choices about the team. Who's the right person to manage this project at this time? Is it an early-stage company or a funded one? Is it in a regulated industry? These questions determine team assembly. This is my framework, and I'll be teaching classes on it soon. It's also the focus of my next book.

Rob: That's awesome.

Richard: The book will describe this framework in more detail.

The Lesson Kristy Taught

Rob: Very cool. I've done some research on you and will look out for your upcoming work. I appreciate you joining this meeting, especially today, given the anniversary of your wife's passing. Could you share something about her that you’d like people to know?

Richard: Yeah. Kristy taught us the importance of humor in life.

Life throws a lot at you, and it's not supposed to be fair. It's supposed to be messy and chaotic. Kristy reminded us to take it with a light heart, to giggle at ourselves, and not to be too serious all the time. What matters is bringing family and friends close and doing wonderful things together. Last year, I took my boys traveling for four months. We had unique experiences together. Kristy was about staying true to the values of family and friends first. That's how we live now. You can have material things, but without those values, life can be pretty dull. She passed away at 39, and other close ones also passed away young. If you think you're going to live forever, unfortunately, the evidence doesn't support that. You've got to live for the moment.

Life throws a lot at you, and it's not supposed to be fair. It's supposed to be messy and chaotic.

You have to have a sense of humor about life, just go for it and have a good time.


I really enjoyed speaking with Richard. I learned so much. here's a few key things I want to apply in my own life and work:

  1. Adopt the 'Terrain, Tools, and Team' Framework: Banfield emphasizes the importance of understanding the specific context ('Terrain') you're operating in, choosing the right methodologies and technologies ('Tools') for your projects, and assembling a team that's well-suited for the task at hand ('Team'). This holistic approach ensures that every aspect of product management is tailored to the unique challenges and opportunities of each project.

  2. Value of Diverse Experiences: Banfield's transition from marine biology to product management illustrates the power of a diverse background. Aspiring PMs should embrace varied experiences and skills, as these can lead to innovative problem-solving and a broader perspective in managing products.

  3. Embrace Experimentation and Adaptability: Drawing on his scientific background, Banfield highlights the importance of experimentation in product management. He suggests approaching each challenge with a hypothesis-testing mindset, being adaptable to changing circumstances, and learning from each success and failure.

These insights from Banfield's career journey and philosophy provide a roadmap for all of us who manage products looking to excel. By incorporating these principles into your approach, you can develop a more adaptable, well-rounded, and innovative style of management, setting a strong foundation for a successful career in product management.

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